The invention relates to a substance for dyeing keratinic fibers, in particular human hair, which comprises specific 1-substituted 1,2-dihydro-3,4,6-trimethyl-2-oxopyrimidinium derivatives in combination with selected aldehydes as reactive carbonyl compound, to the use of this combination in substances for dyeing keratinic fibers, for freshening up the color or nuancing keratinic fibers which have already been dyed, and to a method of dyeing keratinic fibers, in particular human hair.
For dyeing keratinic fibers, either direct dyes or oxidation dyes, which arise as a result of oxidative coupling of one or more developer components with one another or with one or more coupler components, are generally used. Coupler and developer components are also referred to as oxidation dye precursors.
The developer components used are usually primary aromatic amines with a further free or substituted hydroxy or amino group located in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives, and 2,4,5,6-tetraminopyrimidine and derivatives thereof.
Specific representatives are, for example, p-phenylenediamine, p-tolylenediamine, 2,4,5,6-tetraminopyrimidine, p-aminophenol, N,N-bis(2-hydroxyethyl)-p-phenylenediamine, 2-(2,5-diaminophenyl)ethanol, 2-(2,5-diaminophenoxy)ethanol, 1-phenyl-3-carboxyamido-4-aminopyrazol-5-one, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
The coupler components used are usually m-phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones, m-aminophenols and substituted pyridine derivatives. Suitable coupler substances are, in particular, α-naphthol, 1,5-, 2-7- and 1,7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2,4-diaminophenoxyethanol, 2-amino-4-(2-hydroxyethylamino)anisole (Lehmann's Blue), 1-phenyl-3-methylpyrazol-5-one, 2,4-dichloro-3-aminophenol, 1,3-bis(2,4-diaminophenoxy)propane, 2-chlororesorcinol, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 3-amino-6-methoxy-2-methylaminopyridine and 3,5-diamino-2,6-dimethoxypyridine.
With regard to further customary dye components, reference is made expressly to the “Dermatology” series, published by Ch. Culnan, H. Maibach, Verlag Marcel Dekker Inc., New York, Basle, 1986, vol. 7, Ch. Zviak, The Science of Hair Care, chapter 7, pages 248-250 (Direct Dyes) and chapter 8, pages 264-267 (Oxidation Dyes), and the “European Inventory of Cosmetic Raw Materials”, 1996, published by the European Commission, obtainable in disk from the Bundesverband der deutschen Industrie- und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemittel e.V., Mannheim.
With oxidation dyes, although it is possible to achieve intense colorations with good fastness properties, the development of the color takes place, however, inter alia under the influence of oxidizing agents such as, for example, H2O2, which in some cases can result in damage to the fibers. The provision of oxidation hair colorations in the red range with adequate fastness properties, in particular with very good washing- and rubbing-fastnesses, continues to be problematic. Furthermore, some oxidation dye precursors or certain mixtures of oxidation dye precursors can sometimes have a sensitizing effect in people with sensitive skin. Direct dyes are applied under more gentle conditions, but their disadvantage is that the colorations often only have inadequate fastness properties.
The publication by H. Baumann et al., Liebigs Ann. Chem., 1968, 717, 124-136 describes reactions of pyrimidones as methylene bases. A hair colorant comprising 1,2-dihydro-2-oxopyrimidinium derivatives or the use of the disclosed hemicyanines for dyeing keratinic fibers is not proposed here.
In the German patent application DE-A1-2047431, cationic methine dyes for dyeing anionically modified fibers, such as acidically modified polyesters or acrylonitrile polymers are described. To synthesize the cationic methine dyes, use is made, inter alia, of 3,4-dihydro-3-methyl-4-methylenequinazol-2-one and 1,3,6-trimethyl-4-methylenepyrimidin-2-one and, mandatorily, terephthalaldehyde.
The German patent application DE-A1-2165913 proposes a method of producing bleaching-out formers using photosensitive dyes. The claimed photosensitive dyes belong to the class of pyrimidone and thiopyrimidone dyes.
The German patent application DE-A1-102 41 076 proposes 1,2-dihydro-2-oxopyrimidinium derivatives in combination with reactive carbonyl compounds as substances for dyeing keratin fibers. However, these substances are still in need of improvement with regard to the fastness of the colorations thereby achieved, in particular the fastness to light and washing.
In the knowledge of the printed specification DE-A1-2165913, it is known that the dyes based on pyrimidones are photosensitive. Although it was found in DE-A1-102 41 076 that these dyes are highly suitable for dyeing hair also with regard to the light fastnesses, it was precisely the parameter of light fastness which was still in need of improvement. It is thus an object of the present invention to provide colorants for keratinic fibers, in particular human hair, which, with regard to color depth, gray coverage and fastness properties, such as, for example, light-, rubbing- and washing-fastness, and also perspiration- and cold-wave-fastness, especially washing- and light-fastness, are superior in qualitative terms to the dyes according to DE-A1-102 41 076. Moreover, the colorants must have no or only a very slight sensitization potential.